Aromatic substituted methyl esters of hydrazoic acid as insecticides



' Patented June 9, 1942 UNITED STATES PATENT oFFicE- AROMATIC SUBSTITUTED METHYL ESTERS OF HYDRAZOIC ACID AS INSECTICIDES Ingenuin Hechenbleikner, Stamford, Conn., as-

signor to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Application May 31, 1940, Serial No. 338,046

4 Claims.

The present invention relates to insecticides and more particularly to a class of compounds which are especially effective as contact poisons for the control of insect pests.

The invention is based upon the discovery that aromatic substituted methyl esters of hydrazoic acid of the general formula:

in which R is an aryl radical, and R and R represent hydrogen or an aryl radical, possess high insecticidal activity against insets which are particularly diflicult to exterminate, for example, the red spider, and that such activity is attained without any substantial harmful or detrimental action on the vegetation infested with the insect.

The following examples illustrate in detail the preparation of representative compounds of the invention. Materials employed are in parts by weight. 4

Example 1 Parts Triphenylmethyl chloride 5 Sodium azide 1.2 Acetone 40 were mixed together in a vessel and heated upon a steam bath underreflux for 1 hour. The solution was poured into water, extracted with ether and dried over sodium sulfate. The ether was evaporated upon a steam bath leaving triphenyl azido methane as a colorless crystalline residue. After recrystallization from petroleum ether the product had a melting point of 64 C Ea'ample A mixture of parts of l-naphthylmethyl chloride, 5 parts of sodium azide, and 40 parts of absolute alcohol was heated in a vessel under reflux upon a steam bath for 3 hours. The reaction mixture was poured into water, extracted with ether and dried over sodium sulfate. After removal of the ether, the l-naphthyl azido methane was recovered as a colorless odorless mobile liquid boiling at 123 C. at less than 1 mm. pressure.

Spray solutions were prepared by dissolving the above insecticidal compounds in a solvent medium consisting of 65% acetone and 35% water. The following table showsthe kills obtained under comparable condition when the sprays were applied to the citrus red spider.

Compound Dilution g fi o 10 l-nalpahthyl azido methane o A 100% kill of the red spider eggs is obtained in conjunction with the 100% kill of the active forms.

It is believed that the l-naphthyl azido methane is a new compound.

Similarly, other aromatic substituted methyl esters of hydrazoic acid, for example, phenyl azido methane, diphenyl azido methane, di-lnaphthyl azido methane, tri-l-naphthyl azido methane, l-naphthyl phenyl azido methane, l-naphthyl diphenyl azido methane, and di-l- .naphthyl phenyl azido methane having insectistricted solely by the scope of the appended claims.

I claim: 1. An insecticidal composition including a toxic 40 amount of a compound of the general formula:

in which R is an aryl radical and R and R" are selected from the group consisting of hydrogen and an aryl radical.

2. An insecticidal composition including a toxic amount of diphenyl azido methane.

3. An insecticidal composition including a toxic amount of triphenyl azido methane.

4. An insecticidal composition including a toxic amount of 'l-naphthyl azido methane.

INGENUIN HECHENBLEIKNER.

cidal activity may be prepared as in the above. 

